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Cheap flights from Toronto to Chicago from C$ 172

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Toronto to Chicago departing on 14/7. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
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Mon 27/5
Mon 3/6

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Easily compare round-trip flights from Toronto to Chicago

Below you can see the best fares for your round-trip flight route over the next three months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Toronto to Chicago by changing tabs
Porter Airlines
7 Jun.
YTZ9:20 a.m.Toronto Island
1h 47m
MDW10:07 a.m.Chicago Midway
13 Jun.
MDW8:00 a.m.Chicago Midway
1h 42m
YTZ10:42 a.m.Toronto Island
Multiple Airlines
27 Jun.
YYZ7:00 a.m.Toronto Pearson Intl
1h 57m
ORD7:57 a.m.Chicago O'Hare Intl
2 Jul.
ORD6:00 a.m.Chicago O'Hare Intl
1h 48m
YYZ8:48 a.m.Toronto Pearson Intl
Air Canada
8 Sep.
YYZ9:00 a.m.Toronto Pearson Intl
1h 53m
ORD9:53 a.m.Chicago O'Hare Intl
27 Sep.
ORD6:00 a.m.Chicago O'Hare Intl
1h 37m
YYZ8:37 a.m.Toronto Pearson Intl
United Airlines
19 Jun.
YYZ11:00 a.m.Toronto Pearson Intl
2h 02m
ORD12:02 p.m.Chicago O'Hare Intl
26 Jun.
ORD9:45 p.m.Chicago O'Hare Intl
9h 13m
1 stop
YYZ7:58 a.m.Toronto Pearson Intl
American Airlines
4 Jun.
YYZ1:20 p.m.Toronto Pearson Intl
1h 55m
ORD2:15 p.m.Chicago O'Hare Intl
11 Jun.
ORD5:30 a.m.Chicago O'Hare Intl
8h 29m
1 stop
YYZ2:59 p.m.Toronto Pearson Intl
Delta
11 Jun.
YYZ6:04 a.m.Toronto Pearson Intl
3h 44m
1 stop
MDW8:48 a.m.Chicago Midway
29 Jun.
MDW5:45 p.m.Chicago Midway
4h 05m
1 stop
YYZ10:50 p.m.Toronto Pearson Intl

Find the cheapest one-way flights from Toronto to Chicago

If you're looking for one-way flights from Toronto to Chicago, view some of our deals below provided by Air Canada and Porter Airlines
Porter Airlines
14 Jul.
YTZ10:30 a.m.Toronto Island
1h 47m
MDW11:17 a.m.Chicago Midway
Multiple Airlines
3 Jun.
YYZ6:30 a.m.Toronto Pearson Intl
28h 25m
1 stop
ORD9:55 a.m.Chicago O'Hare Intl
Air Canada
22 Jun.
YYZ9:00 a.m.Toronto Pearson Intl
1h 54m
ORD9:54 a.m.Chicago O'Hare Intl

Search last-minute flights to Chicago from Toronto

Find and compare round-trip flight prices for your last-minute flight from Toronto to Chicago
Porter Airlines
31 May
YTZ3:30 p.m.Toronto Island
1h 47m
MDW4:17 p.m.Chicago Midway
5 Jun.
MDW11:05 a.m.Chicago Midway
1h 42m
YTZ1:47 p.m.Toronto Island
Multiple Airlines
28 May
YYZ7:45 a.m.Toronto Pearson Intl
15h 01m
1 stop
ORD9:46 p.m.Chicago O'Hare Intl
29 May
ORD5:00 a.m.Chicago O'Hare Intl
15h 15m
1 stop
YYZ9:15 p.m.Toronto Pearson Intl
Air Canada
1 Jun.
YYZ2:00 p.m.Toronto Pearson Intl
1h 54m
ORD2:54 p.m.Chicago O'Hare Intl
4 Jun.
ORD6:00 a.m.Chicago O'Hare Intl
1h 45m
YYZ8:45 a.m.Toronto Pearson Intl
Delta
1 Jun.
YYZ5:59 p.m.Toronto Pearson Intl
3h 56m
1 stop
ORD8:55 p.m.Chicago O'Hare Intl
4 Jun.
ORD9:36 a.m.Chicago O'Hare Intl
7h 44m
1 stop
YYZ6:20 p.m.Toronto Pearson Intl
United Airlines
31 May
YYZ7:43 p.m.Toronto Pearson Intl
4h 37m
1 stop
ORD11:20 p.m.Chicago O'Hare Intl
5 Jun.
ORD12:00 p.m.Chicago O'Hare Intl
1h 52m
YYZ2:52 p.m.Toronto Pearson Intl
American Airlines
1 Jun.
YYZ6:00 a.m.Toronto Pearson Intl
7h 08m
1 stop
ORD12:08 p.m.Chicago O'Hare Intl
8 Jun.
ORD8:30 a.m.Chicago O'Hare Intl
9h 08m
1 stop
YYZ6:38 p.m.Toronto Pearson Intl

Air Canada flights from Toronto to Chicago

Our best Air Canada deals on Toronto to Chicago flight tickets
Air Canada
8 Sep.
YYZ9:00 a.m.Toronto Pearson Intl
1h 53m
ORD9:53 a.m.Chicago O'Hare Intl
27 Sep.
ORD6:00 a.m.Chicago O'Hare Intl
1h 37m
YYZ8:37 a.m.Toronto Pearson Intl
Air Canada
15 Sep.
YYZ8:05 a.m.Toronto Pearson Intl
1h 56m
ORD9:01 a.m.Chicago O'Hare Intl
18 Sep.
ORD2:00 p.m.Chicago O'Hare Intl
6h 08m
1 stop
YYZ9:08 p.m.Toronto Pearson Intl
Air Canada
4 Oct.
YYZ7:00 a.m.Toronto Pearson Intl
1h 56m
ORD7:56 a.m.Chicago O'Hare Intl
7 Oct.
ORD7:26 a.m.Chicago O'Hare Intl
1h 32m
YYZ9:58 a.m.Toronto Pearson Intl

United Airlines flights from Toronto to Chicago

Our best United Airlines deals on Toronto to Chicago flight tickets
United Airlines
19 Jun.
YYZ11:00 a.m.Toronto Pearson Intl
2h 02m
ORD12:02 p.m.Chicago O'Hare Intl
26 Jun.
ORD9:45 p.m.Chicago O'Hare Intl
9h 13m
1 stop
YYZ7:58 a.m.Toronto Pearson Intl
United Airlines
10 Sep.
YYZ7:43 p.m.Toronto Pearson Intl
4h 31m
1 stop
ORD11:14 p.m.Chicago O'Hare Intl
26 Sep.
ORD7:26 a.m.Chicago O'Hare Intl
1h 32m
YYZ9:58 a.m.Toronto Pearson Intl
United Airlines
7 Jun.
YYZ4:00 p.m.Toronto Pearson Intl
2h 02m
ORD5:02 p.m.Chicago O'Hare Intl
11 Jun.
ORD9:45 p.m.Chicago O'Hare Intl
9h 15m
1 stop
YYZ8:00 a.m.Toronto Pearson Intl

How to get the cheapest flight ticket from Toronto to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly from Toronto to Chicago?

April. The cheapest time of year to fly to Chicago from Toronto is April. The most expensive is September.

What is the cheapest day to depart Toronto for Chicago?

Saturday. The cheapest day of the week is typically Saturday. The most expensive is typically Sunday

When is the cheapest time to fly from Toronto to Chicago?

In the evening. Toronto to Chicago flights are approximately 5% more expensive at noon than in the evening

What is the cheapest airline that flies to Chicago from Toronto?

Air New Zealand. ANA, Air New Zealand, and Alaska Airlines are the most popular carriers operating from Toronto to Chicago

What is the cheapest Toronto to Chicago flight route?

Toronto Island - Chicago Midway. Fly from Toronto Island to Chicago Midway for the best Toronto - Chicago flight prices

How far in advance should you book Toronto to Chicago flights?

37 days before. The cheapest time to buy a flight from Toronto to Chicago is approximately 37 days to departure

How many flights depart from Toronto to Chicago on average per day?

54 flights are operational weekly from Toronto to Chicago as of May 2024. The most popular departure time for this route is 6:00a.m., with 49% of flights per day taking off in the afternoon.

How many flights depart from Toronto to Chicago on average per week?

379 flights are operational weekly from Toronto to Chicago as of May 2024. The most popular departure day for this route is Friday, with 17% of flights per week taking off on this day.

What cabin class options are available on Toronto to Chicago flights?

There are 4 cabin classes available to choose from on Toronto to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Toronto to Chicago flights?

No. A direct flight is the cheapest option for a flight between Toronto to Chicago.

Cheap Toronto to Chicago (YTO to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Toronto to Chicago

Best price found

C$ 172

Fastest flight time

1h 47m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Toronto in the past 72 hours is C$ 172. The best round-trip flight deal from Toronto to Chicago found on momondo in the last 72 hours is C$ 284.
The fastest flight from Toronto to Chicago takes 1h 47m
Direct flights go from Toronto to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

  • How far is Toronto to Chicago by plane?

    Chicago is 700.6 km away from Toronto. Flights usually cover this in 1h 47m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Toronto to Chicago?

    Prices for flights from Toronto to Chicago are updated daily.

  • How many operators does momondo search for flights from Toronto to Chicago?

  • How old do you have to be to fly from Toronto to Chicago?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Toronto to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.


Best airlines flying from Toronto to Chicago

Compare and see reviews for airlines that fly from Toronto to Chicago with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom C$ 259Free CancellationRating
7.4
10,870 reviews
Search United Airlines flights
Porter AirlinesPriceFrom C$ 264Free CancellationRating
7.4
410 reviews
Search Porter Airlines flights
Air CanadaPriceFrom C$ 291Free CancellationRating
7.0
6,954 reviews
Search Air Canada flights
Air New ZealandPriceFrom C$ 299Free CancellationRating
8.2
617 reviews
Search Air New Zealand flights
ANAPriceFrom C$ 323Free CancellationRating
8.4
918 reviews
Search ANA flights
Alaska AirlinesPriceFrom C$ 329Free CancellationRating
8.0
9,171 reviews
Search Alaska Airlines flights
DeltaPriceFrom C$ 347Free CancellationRating
8.0
10,585 reviews
Search Delta flights
American AirlinesPriceFrom C$ 353Free CancellationRating
7.3
14,421 reviews
Search American Airlines flights
WestJetPriceFrom C$ 433Free CancellationRating
7.5
2,898 reviews
Search WestJet flights
WestJet EncorePriceFrom C$ 460Free CancellationRating
8.1
43 reviews
Search WestJet Encore flights
  • ANA Flights From Toronto to Chicago

    Across 20 ANA flights from Toronto to Chicago this week, the average price was C$ 322, with the best ANA deals starting from C$ 237 round-trip. 918 users have rated ANA on momondo, with an average score of 8.4/10.

  • Air New Zealand Flights From Toronto to Chicago

    Air New Zealand is also a popular choice for this route. Air New Zealand flight deals for Toronto to Chicago start from as low as C$ 219 round-trip, depending on your selected dates, with average Air New Zealand deals seen on momondo around C$ 241. Air New Zealand operates 39 flights to Chicago from Toronto in an average week. Users have rated it 8.2/10 across 617 reviews.


Why use momondo?

Why should I use momondo to find a flight deal from Toronto to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Toronto.

Can I find flights from Toronto to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from Toronto on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Toronto to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Toronto.

I’m not ready to book a flight from Toronto to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Toronto to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.


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From?
To?
Mon 27/5
Mon 3/6
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Find better results for your trip to the United States

Fly into one of these airports located in Chicago
Airports listed have a maximum distance of 25.6 km from Chicago